Benzaldehyde → (1-(Benzylamino)cyclopropyl)methanol

HRID 584173Notes

Reaction equation

HRID 584173 reaction equation
Cl.[NH2:2][C:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl.C(N(CC)CC)C>[CH2:8]([NH:2][C:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 14146222(1-Aminocyclopropyl)methanol hydrochloride

Product 1

HCID 22342704(1-(Benzylamino)cyclopropyl)methanolYield 40.6%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 1-amino-1-cyclopropanemethanol hydrochloride (1.1 g), benzaldehyde (945 mg) and triethylamine (1.24 ml) in 1,2-dichloroethane (10 ml), sodium triacetoxyborohydride (5.66 g) was added with ice-cooling over 5 minutes. After being stirred at room temperature for 13 hours, the mixture was poured into aqueous sodium bicarbonate solution and stirred for several hours. The organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure to give 1-(N-benzylamino)-1-cyclopropanemethanol (641 mg).

Workup

  1. additionwas added with ice-
  2. temperaturecooling over 5 minutes
  3. stirringstirred for several hours
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-be6c2d3b1f6244b5b59c20ce25b15832
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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